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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 509891Generated: October 25, 2026

Sodium hydride → 2-(8-bromo-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(piperidin-1-yl)ethanone

https://huagongshe.com/reaction/509891

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
Reactant8-Bromo-2,3,4,5-tetrahydro-2-methyl-1H-pyrido(4,3-b)indoleHCID 199816—
Reactant2-Chloro-1-piperidine-1-yl-ethanoneHCID 222312—
SolventTetrahydrofuranHCID 8028—
SolventHexaneHCID 8058—
Product2-(8-bromo-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(piperidin-1-yl)ethanoneHCID 4477191351.2%

Reaction Steps

Sodium hydride (0.6 g, 15 mmol) washed with hexane for removal of oil and dried under vacuum. Then sodium hydride was taken in THF. To this solution 8-bromo-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (2 g, 7.5 mmol) in THF was added drop wise at 0° C. Then reaction mixture stirred for 0.5 h. The solution of 2-chloro-1-(piperidin-1-yl)ethanone (1.8 g, 11.3 mmol) in THF was added drop wise in reaction mixture. Then reaction mixture stirred at rt for 2 h. Reaction was monitored by TLC. After completion of the reaction, reaction mixture quench with ice-water. THF was evaporated and aqueous layer was extracted with ethyl acetate. Organic layer was dried over anhydrous sodium sulphate. The crude compound was washed with hexane and diethyl ether for removal of color impurities then recrystallized by using methanol to gives 1.5 g of desired compound then out of that 0.8 g compound was stirred in ethanolic HCl to give HCl salt of 2-(8-bromo-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(piperidin-1-yl)ethanone.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09096591B2
Source datasetuspto-grants-2015_08
ORD IDord-49177dfb037c485d9b782290c2518a05
Source noteuspto-grants-2015_08